US4404000A - Middle and/or heavy distillate composition having good flow property and filterability - Google Patents

Middle and/or heavy distillate composition having good flow property and filterability Download PDF

Info

Publication number
US4404000A
US4404000A US06/411,807 US41180782A US4404000A US 4404000 A US4404000 A US 4404000A US 41180782 A US41180782 A US 41180782A US 4404000 A US4404000 A US 4404000A
Authority
US
United States
Prior art keywords
copolymer
ethylene
heavy distillate
filterability
weight
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US06/411,807
Other languages
English (en)
Inventor
Yoshiki Toyoshima
Sumio Hara
Masaki Nakazyo
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sumitomo Chemical Co Ltd
Original Assignee
Sumitomo Chemical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Co Ltd filed Critical Sumitomo Chemical Co Ltd
Assigned to SUMITOMO CHEMICAL COMPANY, A CORP. OF JAPAN reassignment SUMITOMO CHEMICAL COMPANY, A CORP. OF JAPAN ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: TOYOSHIMA, YOSHIKI, HARA, SUMIO, NAKAZYO, MASAKI
Application granted granted Critical
Publication of US4404000A publication Critical patent/US4404000A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/192Macromolecular compounds
    • C10L1/195Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/192Macromolecular compounds
    • C10L1/195Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/196Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof
    • C10L1/1963Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and a carboxyl group or salts, anhydrides or esters thereof homo- or copolymers of compounds having one or more unsaturated aliphatic radicals each having one carbon bond to carbon double bond, and at least one being terminated by a carboxyl radical or of salts, anhydrides or esters thereof mono-carboxylic
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/192Macromolecular compounds
    • C10L1/195Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • C10L1/197Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid
    • C10L1/1973Macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds derived from monomers containing a carbon-to-carbon unsaturated bond and an acyloxy group of a saturated carboxylic or carbonic acid mono-carboxylic

Definitions

  • This invention relates to middle or heavy distillate compositions of petroleum having a good flow property and filterability.
  • Light and heavy oils thereof can cause serious troubles under low temperature conditions in winter or in other cold circumstances, on account of a marked decrease in fluidity due to deposition of wax fractions contained in these oils.
  • a strainer set up in a light oil feed line for a diesel engine is blinded by deposition of wax fractions in the light oil under a cold condition in winter and thereby the supply of the oil is stopped or further at a lower temperature the operation of diesel engine becomes impossible on account of a complete loss of fluidity of the oil.
  • lighter distillates of oil such as kerosene are more expensive than light or heavy oil, so that this method cannot be said to be economical. It also cannot be regarded as a desirable method, from the viewpoint of effective utilization of oil source under the present conditions that there is a worldwide trend of increasing proportion of heavier crude oil supply while demands for lighter fractions of oil are increasing.
  • Another method for this purpose is to add a fluidity improver, for which chemical synthetic products are used in almost all the cases.
  • the role of these fluidity improvers is to stabilize the wax deposit in microcrystalline form, thereby preventing its crystal growth.
  • Various fluidity improvers have been proposed and actually are added to fuel oils, exhibiting a great effect.
  • the following compounds are well known as typical fluidity improvers for fuel oils: Copolymers of ethylene with alkyl esters of unsaturated carboxylic acids or vinyl esters of saturated carboxylic acids, polyacrylates, alkylnaphthalenes, and alkenyl succinates and derivative of the succinates.
  • this invention provides a middle and/or heavy distillate composition having a good flow property and filterability, comprising a fuel oil of varying proportions of middle and/or heavy distillate of petroleum and 10-2000 ppm, based on the fuel oil, of a mixture of 1-99% by weight of (A) a copolymer of ethylene with an alkoxyalkyl acrylate or methacrylate represented by the formula, ##STR2## wherein R 1 represents hydrogen or C 1 -C 2 alkyl and R 2 is -C m H 2m -O-C n H 2n+1 , m and n each being an integer of 1-4, and 99-1% by weight of (B) a copolymer of ethylene with a vinyl ester of saturated carboxylic acid and/or an alkyl ester of ethylenic unsaturated carboxylic acid (hereinafter, the former copolymer is referred to briefly as ethylene copolymer (A) and the latter copolymer as ethylene copolymer
  • the middle and/or heavy distillate of petroleum in this invention means fractions of b.p. approximately 130°-450° C. obtained by atmospheric or vacuum distillation of crude oil, which generally include light oil and so-called A-heavy oil (corresponding to first class heavy oil according to JIS).
  • the ethylene copolymers (A) and (B) used in this invention can be prepared by known processes, for example, free radical types of bulk polymerization, emulsion polymerization, and solution polymerization.
  • the free radical type of bulk polymerization is industrially advantageous, which does not need solvent or some other materials.
  • ethylene and a comonomer shown below can be polymerized by using a continuous type of high pressure polymerization apparatus at a pressure of 500-4000 kg/cm 2 and a temperature of 100°-300° C.
  • a free radical initiator and a polymerization regulator for example, as the initiator, an azo group catalyst such as ⁇ , ⁇ '-azobisisobutyronitrile or a peroxide type catalyst such as di-t-butyl peroxide, hydrogen peroxide, diethyl peroxide, persuccinic acid, alkali metal persulfate, alkaline earth metal persulfate, or ammonium persulfate, and as the polymerization regulator, propane, butane, propylene, butene, propionaldehyde, methyl ethyl ketone, tetrahydrofuran, n-butyraldehyde, acetone, or cyclohexanone.
  • an azo group catalyst such as ⁇ , ⁇ '-azobisisobutyronitrile or a peroxide type catalyst such as di-t-butyl peroxide, hydrogen peroxide, diethyl peroxide, persuccinic acid, al
  • the number average molecular weight and copolymer composition of the ethylene copolymer can be readily controlled to desired values by proper selection of polymerization conditions, for instance, reaction pressure, temperature, catalyst concentration, concentration of chain transfer agent (polymerization regulator), comonomer concentration, etc.
  • alkoxyalkyl acrylates or methacrylates represented by the formula, ##STR3## (R 1 and R 2 are as defined above) include ethoxymethyl acrylate, 2-methoxyethyl acrylate, 2-ethoxyethyl acrylate, 2-ethoxypropyl acrylate, 2-methoxyethyl methacrylate, 2-ethoxyethyl methacrylate, 2-propoxyethyl methacrylate, and 2-butoxyethyl methacrylate, of which 2-methoxyethyl acrylate and 2-ethoxyethyl methacrylate are preferable.
  • the ethylene copolymer (A) has a number average molecular weight of desirably 700-5000, preferably 1000 to 4000 and an acrylate or methacrylate monomer unit content of desirably 5-40%, preferably 10-30%, by weight.
  • the comonomers to be copolymerized with ethylene into the ethylene copolymers (B) are alkyl esters of ethylenic unsaturated carboxylic acids or vinyl esters of saturated carboxylic acids including fatty acid esters such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl octanoate and vinyl stearate and acrylates or methacrylates such as methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, octyl acrylate, octyl methacrylate, dodecyl acrylate, dodecyl methacrylate, stearyl acrylate, and stearyl methacrylate, of which vinyl acetate is most suited.
  • the ethylene copolymer (B) has a number average molecular weight of desirably 700-5000, preferably 1000-4000, and a comonomer unit content of desirably 5-50%, preferably 10-40%, by weight.
  • the mixtures of ethylene copolymers (A) and (B) consist of 1-99%, preferably 10-90% by weight of the ethylene copolymer (A) and 99-1%, preferably 90-10%, by weight of the ethylene copolymer (B). If proportion of the ethylene copolymer (A) or (B) is less than 1% by weight or more than 99% by weight, the synergistic effect of the combined use is as little as within the range of error and it becomes therefore meaningless to have trouble to mix the two copolymers.
  • Suitable amounts of the mixture added to the fuel oil are 10-2000 ppm, preferably 30-1000 ppm, based on the oil, by weight. With the amount less than 10 ppm, almost no effect of the addition can be expected. The amount exceeding 2000 ppm results in worse economy relative to the effect obtained.
  • the two copolymers may be added either after being mixed or separately without the previous mixing. They may be added also in the form of concentrated solution in a suitable solvent selected from aliphatic hydrocarbons, aromatic hydrocarbons, etc.
  • ethylene copolymers may be used some usual additives for petroleum distillate fuel oils, such as rust inhibitors, antioxidants, antistatic agents, and anticorrosives, and if necessary, a pour point depressant of other types.
  • Fuel oil compositions shown in Table 4 were prepared by adding different ethylene copolymers singly or in mixture to the fuel oil (1) or (2) shown in Table 3, and the fluidity and filterability thereof were evaluated.
  • Cold filter plugging point Measured according to the method reported in "Cold Filter Plugging Point of Distillate Fuels", IP-309, 1976, England, by using a 44-micron stainless steel screen.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Liquid Carbonaceous Fuels (AREA)
US06/411,807 1981-09-03 1982-08-26 Middle and/or heavy distillate composition having good flow property and filterability Expired - Lifetime US4404000A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP56139290A JPS5840391A (ja) 1981-09-03 1981-09-03 燃料油の低温流動性改良方法

Publications (1)

Publication Number Publication Date
US4404000A true US4404000A (en) 1983-09-13

Family

ID=15241833

Family Applications (1)

Application Number Title Priority Date Filing Date
US06/411,807 Expired - Lifetime US4404000A (en) 1981-09-03 1982-08-26 Middle and/or heavy distillate composition having good flow property and filterability

Country Status (7)

Country Link
US (1) US4404000A (fr)
EP (1) EP0074208B1 (fr)
JP (1) JPS5840391A (fr)
AU (1) AU548967B2 (fr)
CA (1) CA1180894A (fr)
DE (1) DE3267303D1 (fr)
SU (1) SU1217262A3 (fr)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4509954A (en) * 1983-02-16 1985-04-09 Nippon Oil And Fats Company, Ltd. Method for improving cold flow of fuel oils
DE3613247A1 (de) * 1986-04-19 1987-10-22 Roehm Gmbh Konzentrierte emulsionen aus ethylen-vinylester-copolymeren
US4746327A (en) * 1985-03-25 1988-05-24 Standard Oil Company (Indiana) Ethylene-unsaturated, ester-substituted olefin terpolymer flow improvers
US4802892A (en) * 1985-09-24 1989-02-07 Mitsubishi Petrochemical Co., Ltd. Fuel oil additive and fuel oil having improved flowability
US5718734A (en) * 1992-06-30 1998-02-17 Exxon Chemical Patents Inc. Oil additives and compositions
US5743923A (en) * 1992-10-26 1998-04-28 Exxon Chemical Patents Inc. Oil additives and compositions
US6638325B1 (en) * 1992-06-30 2003-10-28 Infineum International Ltd. Oil additives and compositions
WO2004106471A1 (fr) * 2003-05-27 2004-12-09 Basf Aktiengesellschaft Compositions de combustibles presentant de meilleures proprietes d'ecoulement a froid
US20060252608A1 (en) * 2005-03-14 2006-11-09 Kang Brian J Response measurement device
EP0648257B2 (fr) 1992-06-30 2007-05-23 ExxonMobil Chemical Patents Inc. Compositions et additifs pour le mazout
US20110118159A1 (en) * 2003-12-04 2011-05-19 Basf Aktiengesellschaft Fuel oil compositions with improved cold flow properties
US20120005951A1 (en) * 2010-07-06 2012-01-12 Basf Se Copolymer with high chemical homogeneity and use thereof for improving the cold flow properties of fuel oils

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3537769A1 (de) * 1985-10-24 1987-04-30 Basf Ag Verwendung von estern von 1-alken-acrylsaeure-copolymerisaten bzw. von 1-alken-methacrylsaeure-copolymerisaten zur verbesserung der fliesseigenschaften von erdoelen
JPS62242229A (ja) * 1986-04-14 1987-10-22 Nec Corp ドツトインパクト・シリアルプリンタ
US5814110A (en) * 1986-09-24 1998-09-29 Exxon Chemical Patents Inc. Chemical compositions and use as fuel additives
JPH0254329A (ja) * 1988-08-18 1990-02-23 Matsushita Graphic Commun Syst Inc 出力装置
JP2538355B2 (ja) * 1989-11-17 1996-09-25 三洋化成工業株式会社 燃料油用流動性向上剤および燃料油組成物
GB9213904D0 (en) * 1992-06-30 1992-08-12 Exxon Chemical Patents Inc Oil additives and compositions
DE19757830C2 (de) 1997-12-24 2003-06-18 Clariant Gmbh Brennstofföle mit verbesserter Schmierwirkung
DE19823565A1 (de) * 1998-05-27 1999-12-02 Clariant Gmbh Mischungen von Copolymeren mit verbesserter Schmierwirkung
DE19927561C1 (de) 1999-06-17 2000-12-14 Clariant Gmbh Verwendung hydroxylgruppenhaltiger Copolymere zur Herstellung von Brennstoffölen mit verbesserter Schmierwirkung
DE19927560C2 (de) 1999-06-17 2002-03-14 Clariant Gmbh Brennstoffölzusammensetzung
WO2023076401A1 (fr) * 2021-10-29 2023-05-04 Ecolab Usa Inc. Mélanges de copolymère d'éthylène-acétate de vinyle et d'un copolymère contenant un (méth)acrylate en tant que dépresseurs du point d'écoulement

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3048479A (en) * 1959-08-03 1962-08-07 Exxon Research Engineering Co Ethylene-vinyl ester pour depressant for middle distillates
US3773478A (en) * 1969-03-17 1973-11-20 Exxon Co Middle distillate fuel containing additive combination to increase low temperature flowability
US3792983A (en) * 1968-04-01 1974-02-19 Exxon Research Engineering Co Ethylene and acrylate esters, their preparation and their use as wax crystal modifiers
US3961916A (en) * 1972-02-08 1976-06-08 Exxon Research And Engineering Company Middle distillate compositions with improved filterability and process therefor
US4087255A (en) * 1968-04-01 1978-05-02 Exxon Research & Engineering Co. Copolymers of ethylene and ethylenically unsaturated monomers, process for their preparation and distillate oil containing said copolymers
US4108612A (en) * 1977-04-04 1978-08-22 Exxon Research & Engineering Co. Derivatized ethylene/polar monomer polymers of improved performance
US4108613A (en) * 1977-09-29 1978-08-22 Chevron Research Company Pour point depressants
US4153424A (en) * 1975-03-28 1979-05-08 Exxon Research & Engineering Co. Polymer combinations useful in distillate hydrocarbon oils to improve cold flow properties

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3454378A (en) * 1966-02-04 1969-07-08 Union Carbide Canada Ltd Pour point depressant for middle distillates
GB1112808A (en) * 1966-06-20 1968-05-08 Exxon Research Engineering Co Improved middle distillate fuel composition
DE2407158B2 (de) * 1974-02-15 1976-01-15 Basf Ag, 6700 Ludwigshafen Erdoeldestillat-brenn- oder -treibstoffe

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3048479A (en) * 1959-08-03 1962-08-07 Exxon Research Engineering Co Ethylene-vinyl ester pour depressant for middle distillates
US3792983A (en) * 1968-04-01 1974-02-19 Exxon Research Engineering Co Ethylene and acrylate esters, their preparation and their use as wax crystal modifiers
US4087255A (en) * 1968-04-01 1978-05-02 Exxon Research & Engineering Co. Copolymers of ethylene and ethylenically unsaturated monomers, process for their preparation and distillate oil containing said copolymers
US3773478A (en) * 1969-03-17 1973-11-20 Exxon Co Middle distillate fuel containing additive combination to increase low temperature flowability
US3961916A (en) * 1972-02-08 1976-06-08 Exxon Research And Engineering Company Middle distillate compositions with improved filterability and process therefor
US4153424A (en) * 1975-03-28 1979-05-08 Exxon Research & Engineering Co. Polymer combinations useful in distillate hydrocarbon oils to improve cold flow properties
US4108612A (en) * 1977-04-04 1978-08-22 Exxon Research & Engineering Co. Derivatized ethylene/polar monomer polymers of improved performance
US4108613A (en) * 1977-09-29 1978-08-22 Chevron Research Company Pour point depressants

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4509954A (en) * 1983-02-16 1985-04-09 Nippon Oil And Fats Company, Ltd. Method for improving cold flow of fuel oils
US4746327A (en) * 1985-03-25 1988-05-24 Standard Oil Company (Indiana) Ethylene-unsaturated, ester-substituted olefin terpolymer flow improvers
US4802892A (en) * 1985-09-24 1989-02-07 Mitsubishi Petrochemical Co., Ltd. Fuel oil additive and fuel oil having improved flowability
DE3613247A1 (de) * 1986-04-19 1987-10-22 Roehm Gmbh Konzentrierte emulsionen aus ethylen-vinylester-copolymeren
US4906682A (en) * 1986-04-19 1990-03-06 Rohm Gmbh Ethylene-vinyl ester copolymer emulsions
EP0648257B2 (fr) 1992-06-30 2007-05-23 ExxonMobil Chemical Patents Inc. Compositions et additifs pour le mazout
US5718734A (en) * 1992-06-30 1998-02-17 Exxon Chemical Patents Inc. Oil additives and compositions
US6638325B1 (en) * 1992-06-30 2003-10-28 Infineum International Ltd. Oil additives and compositions
US5743923A (en) * 1992-10-26 1998-04-28 Exxon Chemical Patents Inc. Oil additives and compositions
WO2004106471A1 (fr) * 2003-05-27 2004-12-09 Basf Aktiengesellschaft Compositions de combustibles presentant de meilleures proprietes d'ecoulement a froid
US20110118159A1 (en) * 2003-12-04 2011-05-19 Basf Aktiengesellschaft Fuel oil compositions with improved cold flow properties
US8642521B2 (en) 2003-12-04 2014-02-04 Basf Se Fuel oil compositions with improved cold flow properties
US9605227B2 (en) 2003-12-04 2017-03-28 Basf Se Fuel oil compositions with improved cold flow properties
US10047314B2 (en) 2003-12-04 2018-08-14 Basf Se Fuel oil compositions with improved cold flow properties
US10526558B2 (en) 2003-12-04 2020-01-07 Basf Se Fuel oil compositions with improved cold flow properties
US20060252608A1 (en) * 2005-03-14 2006-11-09 Kang Brian J Response measurement device
US20120005951A1 (en) * 2010-07-06 2012-01-12 Basf Se Copolymer with high chemical homogeneity and use thereof for improving the cold flow properties of fuel oils
US8721744B2 (en) * 2010-07-06 2014-05-13 Basf Se Copolymer with high chemical homogeneity and use thereof for improving the cold flow properties of fuel oils
US9908955B2 (en) 2010-07-06 2018-03-06 Basf Se Copolymer with high chemical homogeneity and use thereof for improving the cold flow properties of fuel oils

Also Published As

Publication number Publication date
AU548967B2 (en) 1986-01-09
DE3267303D1 (en) 1985-12-12
EP0074208B1 (fr) 1985-11-06
JPS5840391A (ja) 1983-03-09
AU8751882A (en) 1983-03-10
EP0074208A2 (fr) 1983-03-16
SU1217262A3 (ru) 1986-03-07
CA1180894A (fr) 1985-01-15
EP0074208A3 (en) 1983-07-27
JPS6241558B2 (fr) 1987-09-03

Similar Documents

Publication Publication Date Title
US4404000A (en) Middle and/or heavy distillate composition having good flow property and filterability
US4713088A (en) Middle distillate compositions with improved cold flow properties
EP0156577B1 (fr) Compositions de distillat moyen avec des caractéristiques d'écoulement à froid
CA1050759A (fr) Kerosene de distillat moyen a ecoulement a froid ameliore par des additifs
US3642459A (en) Copolymers of ethylene with unsaturated esters and oil compositions containing said copolymers
US20040152849A1 (en) Process for the preparation of ethylene copolymers, and their use as additives to mineral oil and mineral oil distillates
US7067599B2 (en) Fuel oil additives and compositions
US6342081B1 (en) Cloud point depressants for middle distillate fuels
GB2207924A (en) Polymeric flow improvers
US4862908A (en) Mineral oils and mineral oil distillates having improved flowability and method for producing same
US3850587A (en) Low-temperature flow improves in fuels
US3008813A (en) Hydrocarbon oils having improved water tolerance
US4419106A (en) Hydrocarbon oils with improved pour points
JP2514199B2 (ja) 液体燃料雲成物
US3832150A (en) Fuel oil with improved low temperature flowability
EP0255345A1 (fr) Compositions de combustibles liquides
US5585337A (en) Hydrocarbon oil compositions having improved cold flow properties
US20010034968A1 (en) Fuel oils based on middle distillates and copolymers of ethylene and unsaturated carboxylic esters
CA1280598C (fr) Distillat moyen ayant un meilleur fluage
US6203583B1 (en) Cold flow improvers for distillate fuel compositions
US3141745A (en) Dehazing polymer-containing hydrocarbon oils
JPS61287985A (ja) 燃料油の低温流動性改良方法
US3346353A (en) Hydrocarbon oils of improved water tolerance and anti-rust characteristics
JP2773316B2 (ja) 重質燃料油組成物
JPS5823885A (ja) 燃料油の低温流動性改良法

Legal Events

Date Code Title Description
AS Assignment

Owner name: SUMITOMO CHEMICAL COMPANY, LIMITED 15 KITAHAMA-5-C

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:TOYOSHIMA, YOSHIKI;HARA, SUMIO;NAKAZYO, MASAKI;REEL/FRAME:004041/0194;SIGNING DATES FROM 19820818 TO 19820819

STCF Information on status: patent grant

Free format text: PATENTED CASE

CC Certificate of correction
CC Certificate of correction
MAFP Maintenance fee payment

Free format text: PAYMENT OF MAINTENANCE FEE, 4TH YEAR, PL 96-517 (ORIGINAL EVENT CODE: M170); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

Year of fee payment: 4

MAFP Maintenance fee payment

Free format text: PAYMENT OF MAINTENANCE FEE, 8TH YEAR, PL 96-517 (ORIGINAL EVENT CODE: M171); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

Year of fee payment: 8

MAFP Maintenance fee payment

Free format text: PAYMENT OF MAINTENANCE FEE, 12TH YEAR, LARGE ENTITY (ORIGINAL EVENT CODE: M185); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

Year of fee payment: 12

FEPP Fee payment procedure

Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY